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[ CAS No. 112-43-6 ] {[proInfo.proName]}

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Chemical Structure| 112-43-6
Chemical Structure| 112-43-6
Structure of 112-43-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 112-43-6 ]

CAS No. :112-43-6 MDL No. :MFCD00004750
Formula : C11H22O Boiling Point : -
Linear Structure Formula :- InChI Key :GIEMHYCMBGELGY-UHFFFAOYSA-N
M.W : 170.29 Pubchem ID :8185
Synonyms :

Calculated chemistry of [ 112-43-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.82
Num. rotatable bonds : 9
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.68
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.1
Log Po/w (XLOGP3) : 4.34
Log Po/w (WLOGP) : 3.29
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 3.44
Consensus Log Po/w : 3.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.04
Solubility : 0.157 mg/ml ; 0.00092 mol/l
Class : Soluble
Log S (Ali) : -4.48
Solubility : 0.00564 mg/ml ; 0.0000331 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.0697 mg/ml ; 0.000409 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 1.95

Safety of [ 112-43-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 112-43-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 112-43-6 ]
  • Downstream synthetic route of [ 112-43-6 ]

[ 112-43-6 ] Synthesis Path-Upstream   1~7

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  • [ 112-43-6 ]
  • [ 53463-68-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3527 - 3539
  • 2
  • [ 112-43-6 ]
  • [ 7766-50-9 ]
YieldReaction ConditionsOperation in experiment
100% With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 2 h; A dichloromethane solution of 10-undecen-1-ol (30, 200 mg,1.17 mmol) was treated with CBr4(403 mg, 1.29 mmol,1.1 eq.) and Ph3P(340 mg, 1.29 mmol, 1.1 eq.) at 0 °C for2 h, and the reaction was quenched by addition of water. Thereaction mixture was extracted with dichloromethane andthe organic layer was dried over anhydrous Na2SO4powder.The organic solvent was evaporated in vacuo to obtain thecrude product. The crude product was used for the furtherreactions without chromatographic purification. The crudeproducts were purified by column chromatography on silicagel to obtain 1-bromo-10-undecene (31, 273 mg, quantitativeyield) [56] as colorless oil.
93% With carbon tetrabromide; triphenylphosphine In dichloromethane at -5 - 20℃; for 14 h; 11-Undecen-1-ol (140 g, 0.82 mol) and CBr4 (300 g, 0.90 mol)were dissolved in CH2Cl2 (500 mL) in Schlenk flask and triphenylphosphine(237 g, 0.90 mol) was then added dropwise over 15 minat 5 C. The systemwas stirred at 5 C for 2 h, and raised to room temperature for 12 h. The solution was concentrated and a white precipitate formed which was removed by filtration. The resultantsolution was fractionally distilled under reduced pressure to get apurified and colorless liquid product (177 g).
82% With N-Bromosuccinimide; triphenylphosphine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5 h; To a solution of undec-10-en-1-ol (0.86 g, 5.0 mmol) in DMF (15 ML) was added triphenylphosphine (1.46 g, 5.6 mmol).The solution was cooled to 0° C. and NBS (0.96 g, 5.4 mmol) was added in portions.After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.5 ML).The solution was diluted with ether (80 ML), washed with water, saturated aqueous NaHCO3 and brine successively.The organic layer was dried and concentrated.The residue was purified by flash chromatography on silica gel, eluding with hexane to afford 11-bromo-undec-1-ene (0.96 g, 82percent) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.79 (1H, m), 4.93 (2H, m), 3.38 (2H, t, J=6.9 Hz), 2.02 (2H, m), 1.83 (2H, m), 1.20-1.55 (12H, m); 13C NMR (75 MHz, CDCl3) δ 139.36, 114.33, 34.27, 33.99, 33.01, 29.57*2, 29.27, 29.09, 28.94, 28.35.
60% With phosphorus tribromide In diethyl ether at -78 - 20℃; Inert atmosphere Phosphorus tribromide (5.3 g, 19.6 mmol, 1.84 ml) was added dropwise to a solution of 10-Undecen-1-ol (10 g, 58.7 mmol) in diethyl ether (100 ml) at −78° C. over a period of 10 min and then the mixture was allowed to warm to room temperature and stirred under Ar overnight. The reaction mixture was quenched with water and the layers were separated. The aqueous layer was extracted with ether (5×30 ml) and the combined organic layers were washed with brine and dried over sodium sulfate. After evaporation of the solvent in vacuo, the crude product was purified by chromatography column on silica gel (hexane) to give pure product 8.2 g (yield: 60percent). 1H NMR (CDCl3) δ 5.85-5.75 (m, 1H), 5.01-4.91 (m, 2H), 3.37-3.41 (t, 2H, J=7.2 Hz), 2.06-1.99 (m, 2H), 1.88-1.81 (m, 2H), 1.39 (br, 2H), 1.29 (br, 10H). 13C NMR (CDCl3) δ 139.4, 114.3.3, 34.2, 34.1, 33.0, 31.8, 29.6, 29.3, 29.1, 29.0, 28.4.

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Reference: [1] Helvetica Chimica Acta, 1926, vol. 9, p. 1086
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  • [ 10035-10-6 ]
  • [ 74036-98-9 ]
  • [ 73641-91-5 ]
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Reference: [1] Helvetica Chimica Acta, 1926, vol. 9, p. 1086
  • 5
  • [ 112-43-6 ]
  • [ 22136-92-1 ]
  • [ 3155-43-9 ]
  • [ 26818-51-9 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 24, p. 6051 - 6054
[2] Tetrahedron, 1985, vol. 41, # 24, p. 6051 - 6054
  • 6
  • [ 67-56-1 ]
  • [ 112-43-6 ]
  • [ 22136-92-1 ]
  • [ 3155-43-9 ]
  • [ 26818-51-9 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 24, p. 6051 - 6054
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  • [ 112-43-6 ]
  • [ 50530-12-6 ]
Reference: [1] Helvetica Chimica Acta, 1926, vol. 9, p. 1086
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